81873-91-8

Basic information

• Product Name: 12-Oxo-ursodeoxycholic acid
• Synonyms: 12-Ketoursodeoxycholic acid;12-Oxo-ursodeoxycholic acid;SF-482
• CAS NO: 81873-91-8
• Molecular Formula: C₂₄H₃₈O₅
• Molecular Weight: 406.56
• Mol File: 81873-91-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 583°C at 760 mmHg
• Flash Point: 320.4°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 5.08E-16mmHg at 25°C
• Refractive Index: 1.55
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly, Heated, Sonicated), DMSO (Sparingly), Ethanol (Slightly, S
• CAS DataBase Reference: 12-Oxo-ursodeoxycholic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 12-Oxo-ursodeoxycholic acid(81873-91-8)
• EPA Substance Registry System: 12-Oxo-ursodeoxycholic acid(81873-91-8)

Safety Data

• Hazardous Substances Data: 81873-91-8(Hazardous Substances Data)

Usage

Uses

12-Ketoursodeoxycholic Acid is an impurity of Ursodeoxycholic Acid (U850000), which is used as an anticholelithogenic.

InChI:InChI=1/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-19,22,25-26H,4-12H2,1-3H3,(H,28,29)/t13-,14+,15-,16-,17+,18+,19+,22+,23+,24-/m1/s1

Upstream product

• 434-13-9 Lithocholic acid 
• 911-40-0 7-ketodeoxycholic acid 

Downstream Products

• 128-13-2 ursodeoxycholic acid 

Relevant articles and documents

Efficient Synthesis of 12-Oxochenodeoxycholic Acid Using a 12α-Hydroxysteroid Dehydrogenase from Rhodococcus ruber

12α-Hydroxysteroid dehydrogenase (12α-HSDH) has the potential to convert cheap and readily available cholic acid (CA) to 12-oxochenodeoxycholic acid (12-oxo-CDCA), a key precursor for chemoenzymatic synthesis of the therapeutic bile acid ursodeoxycholic acid (UDCA). In this work, a native nicotinamide adenine dinucleotide (NAD+)-dependent 12α-hydroxysteroid dehydrogenase (Rr12α-HSDH) from Rhodococcus ruber was identified using a structure-guided genome mining (SSGM) approach, which is based on the structure of cofactor pocket and the conserved nicotinamide cofactor binding motif alignment. Rr12α-HSDH was heterologously overexpressed in Escherichia coli BL21 (DE3), purified and characterized. The purified Rr12α-HSDH showed a high oxidative activity of 290 U mg?1protein toward CA, with a catalytic efficiency (kcat/KM) of 5.10×103 mM?1 s?1. In a preparative biotransformation (100 mL), CA (200 mM, 80 g L?1) was efficiently converted to 12-oxo-CDCA in 1 h, with a 85% isolated yield and a space-time yield (STY) of up to 1632 g L?1 d?1. Furthermore, Rr12α-HSDH was shown to be able to catalyze the oxidation of other 12α-hydroxysteroids at high substrate loads (up to 200 mM), giving the corresponding 12-oxo-hydroxysteroids in 71%–85% yields, indicating the great potential of Rr12α-HSDH as a promising biocatalyst for the synthesis of various therapeutic bile acids. (Figure presented.).

Regioselective oxidation of cholic acid and its 7β epimer by using o-iodoxybenzoic acid

Rational exploration directed by DFT (density functional theory) based atomic Fukui indices, lead to development of regioselective oxidation of cholic acid and its 7β epimer by o-iodoxybenzoic acid. In case of cholic acid only, 7α-hydroxyl underwent oxidation, where as in its 7β epimer the selectivity was towards 12α-hydroxy group. Since these oxidations are the key steps in synthesis of ursodeoxycholic acid starting from cholic acid these findings may be useful in devising a protection free synthetic route.